Denatured alcohol containing 1:3 dioxolane



has customarily been employed, and which will monophenyl-lz4-dioxane be free from methanol. Other objects will herev o 10 inafter appear. H 0 CHfl I have discovered that a cyclic ether selected from the group consisting of 1:4-dioxane, 1:3- dioxane, 1:3-dioxolane and their substitution de- 0 rivatives is an efiective denaturant 'for alcohol. As examples of the substitution derivatives of 1795 (1936)) 15 1:4-dioxane, 1:3-dioxane, and 1:3-dioxolane, I (bromomethyh-l=3-dioxolane may mention the following: H204) I 2:2:5:5-tetrakis (chloromethyl)-l:4-dioxane (L OH.CH2Br 0 I aroma -o 20 I (01110910 CH: (C. A. 17, 1434 (1923)).

Hz1\ /C(CH2C1): 2-chloro-l:3-dloxolane O 1120-0 25 (C. A. 23, 4927 (1929); Ber. 1582-90- (1929)). \0Hg1 2:3-diethoxy-1z4-dloxane ,c 0.

(J. Chem. Soc., 1598 (1933)). 1 CH-(OCHQ 2:2-dimethyl-4-methylene-1:3-dioxo1ane 3 H1O 011(00235) Inc-o o I cwm (C. A. 25, 4849 (1921)). 2 naphthadloxane (c. A. 24, 5024 (1930)). 35

0 0 4-methyl-1:3-dioxolane 1110 C \ZH: OH:.HC0 H: H H: CH2

40 o 0 HI 40 monochlom-mdimne 2:2-dlmethyl-4(5)-hydroxymethyl-1:3-dioxolo 1190 CHCI C(CHs):

E1 Hocmn -o o (C. A. 9, 1469 (1915); J. Chem. Soc. 107, 337

Patented Jan. 7, 1941 Y :DENATURED ALCOHOL CONTAINING 1:3 DIOXOLANE Louis J. Flag. In, Kingsport, Tenn., assignor to Eastman Kodak Company, Rochester, N. Y., a corporation of New Jersey No Drawing. Application May 11, 1938,

' Serial No. 207,354

This invention relates to the denaturing of Y ethyl alcohol, and to alcohol so denatured. 0

It is an object of my invention to provide a H CH denaturant which will render ethyl alcohol con- 5 taining it unfit for use as a beverage, which can- Hi not be economically removed from the alcohol so 0 denatured, which will not render the alcohol unfit for industrial uses in which denatured alcohol 1795 (1936) 2- (dichloromethyl)-2-ethyl-5:5-dimethyI-1:3-dioxo1-4(5)-one (CHa)zC-O C(C2H5).CHCh

2-methyl-1z3-dioxolane HaC-O OILCH:

5-phenyl-4-methyl-1:3-dloxolane CH5.HCO

CH2 CH;.HCO (C. A. 22, 406 (1928)). v I 2-l1ydroxyethyl-lz3-dioxane H CH.CH2CH2OH 2:2-dimethyl-h8-dioxane O HzC C(CHa)2 2-vanillin-5-hydroxy-1:3-dioxane H2O CH.CuHa(OCHa)OH nonc':

(C. A. 16, 2496 (1922) ;'J Am. Chem. Soc. 44,

2-(gamma-acetoxypropyl)-4-methyl1:3-dioxane CH.CH2CH:.CH:.O.CO.CH:

CQCH: (C. A. 23, 4949 (1929)).

5-methoxy-1z3-dioxane ic. A. 23, 99 (1929)).

2=methy1-2-ethyl-1:3-dioxan-5-o1 -Hio owmicim I (on. 23, 4671 (1929)).

. 2-phenyl-1z3-dioxane \GBLCuHu cfia (as; 14, 1111911920) Q -'Z-bmmomethyl-1:3-dioxane [Iv HII C l 0. A.;;17, ;1434 um) 747161923.-

' In denaturing ethyl. alcohol with my novel denaturants, I-' may use from 0.5 'to 5 parts of'the cyclic ether, or even moregper 100*parts of 95% alcohol. My novel denaturants may be used alone in denaturing, or they may'beused in con- J. Am. Chem." Soc. 45,

junction with denaturing materials derived from the destructive distillation of hardwood, such as those which are described .in 'myU. S. Patents Nos. 1,975,090, 1,975,091 and1,975,092. Likewise,

they may be used in'conjunction with amino.

CERTIFICATE OF CORRECTION. Patent No. 2, 221L968. January 7, 191m. LOUIS J. FIGG, JR.

It is hereby certified that error appears in the printed specification of the above numbered patent requiring correction as follows: Page 2, first column, line' 114., for "5pheny1Lp-methy1l:5-dioxo1ane" read :phenyl-5 methy11:5-dioxolane; and that the said Letters Patent should be read with this correction therein that the same may conform to the record of the case in the Patent Office.

Signed and sealed this 1st day of April, A. D. 19in Henry Van Arsdale,

( Acting Commissioner of Patents.

CERTIFICATE OF CORRECTION. Patent No. 2, 2 ,27 ,968m 7 7 January '7, 1911.1.

LOUIS J. FIGG, JR.

It is hereby certified that error appears in the printed specification of the above numbered patent requiring correction as follows: Page 2, first column, line 114., for 5-phenyl-lp-methyl-l:5-dioxolane" read .phenyl- 5- methyl-1:5-dioxolane-; and that the said Letters Patent should be read with this correction therein that the same may conform -to the record of the case in the Patent Office.

Signed and sealed this lst day of April, A. D. 19in.

Henry Van Arsdale,

( Acting Commissioner of Patents. 

